3-METHOXYCYCLOHEXENE synthesis

13synthesis methods

Product Name:3-METHOXYCYCLOHEXENE
CAS Number:4845-04-9
Molecular formula:C7H12O
Molecular Weight:112.17

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Yield: 100%

Reaction Conditions:

with diisobutylaluminium hydride in dichloromethane;toluene at -78; for 1 h;

Steps:

34.1 Step 1: Cyclohex-l-en-l-ylmethanol
Step 1: Cyclohex-l-en-l-ylmethanol To a solution of methyl 1-cyclohexene-l-carboxylate (1.50 mL, 11.0 mmol) in DCM (30 mL) was added diisobutylaluminum hydride (1M solution in toluene; 25 mL, 25 mmol) at -78 °C and the mixture was stirred for 1 h. TLC (3:1 hex:EtOAc) showed that the reaction was then complete. The mixture was quenched with methanol (10 mL) and IN NaOH (10 mL) and then was allowed to stir at rt for 2.5 h. The mixture was extracted with DCM (3x). The combined organic layers were washed with brine, dried over MgSC_t, filtered and concentrated to give cyclohex-l-en-l-ylmethanol (1.3 g, 100%).

References:

MILLENNIUM PHARMACEUTICALS, INC.;DUFFEY, Matthew, O.;ENGLAND, Dylan, B.;HU, Zhigen;ITO, Mitsuhiro;LANGSTON, Steven, P.;MCINTYRE, Charles;MIZUTANI, Hirotake;XU, He WO2015/2994, 2015, A2 Location in patent:Paragraph 00237